1,1'-Carbonyldiimidazole → HCID 86730135, compound

HRID 1850104Notes

Reaction equation

HRID 1850104 reaction equation
[NH2:1][C@@H:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:3][OH:4].C1N=CN([C:22](N2C=NC=C2)=[O:23])C=1>C1COCC1.C([O-])(O)=O.[Na+]>[C:8]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]([C@H:2]2[CH2:3][O:4][C:22](=[O:23])[NH:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66514643HCID 66514643, compound

Product 1

HCID 86730135HCID 86730135, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (S)-2-amino-2-(biphenyl-4-yl)ethanol (171 mg, 0.802 mmol) in THF (12 mL) under argon atmosphere was added CDI (132 mg, 0.814 mmol). The solution was stirred at room temperature for 2 hours. The mixture was diluted with saturated aqueous NaHCO3 solution (40 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with 0.5M aqueous HCl solution (30 mL), brine (40 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was dissolved in DCM and concentrated under reduced pressure to provide crude (S)-4-(biphenyl-4-yl)oxazolidin-2-one (156 mg) as a beige solid, which was used without further purification. LCMS m/z 240.1 (M+H)+, Rt 0.80 min.

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic layers were washed with 0.5M aqueous HCl solution (30 mL), brine (40 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in DCM
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c08d8cdee4b3467b94fe3f5dc4ddd718
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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